In Lowry’s myriad opportunities this season to mention what has made him happiest about his time with the Raptors, he constantly went back to watching his younger teammates improve and grow as players and people. On Tuesday, Lowry was asked who his mentors in leadership were, and he mentioned Alvin Williams, Damon Stoudamire, Chauncey Billups and Ty Lue. (The latter two now coach the Clippers, who have a few of his former teammates, and whose lack of true point guard has been a consistent detriment to their recent championship aspirations. However, the Clippers, assuming they bring back Kawhi Leonard at or near a maximum-value contract, would have to pull off some impressive cap gymnastics to make themselves eligible to complete a sign-and-trade deal.)
Lowry has been close to Fred VanVleet from the start of the undrafted point guard’s time with the Raptors in 2016.
“I just want to pay it forward,” Lowry said. “I’m a big pay-it-forward guy. Hopefully, I can pass it on to the next generation. I don’t take any (credit for) Freddy’s learning to become a better leader. With those things, it’s like, ‘OK, I’m happy to see that.’ Everybody that comes through here has continued to get better. Freddy has taken that leadership role, and he’s gonna be it. He’s gonna be it.”
Which is to say, VanVleet is so obviously the heir apparent in playing style and demeanour that it doesn’t need to be said. As Lowry said, the Raptors are in good hands, and VanVleet, to say little of the rest of the team’s young veterans, is a big reason Lowry believes that. Given that, it would not be a surprise for Lowry to conclude now is a sensible time as any for a baton passing.
There are reasons to think the opposite. Sign-and-trade deals are difficult to pull off, which leaves Miami and maybe Dallas as the only teams likely to have the cap room and type of roster to sign Lowry outright. (You can add the Knicks if you are a true believer.) The only cap on the Raptors’ ability to spend on Lowry will be self-imposed.
To the extent that Lowry is thinking about the Hall of Fame, winding down his career in Toronto would be a more narratively pleasing denouement than playing elsewhere. To that end, you might have heard that the Raptors played this season in Tampa, and it didn’t go well.
“It does play a factor in it because I enjoy the challenge of people counting me out, counting the team out,” Lowry said. “I enjoy that competitive nature, and I wanna challenge myself and see what I can continue to help do and build. But a lot of things will be factored into this summer and this free agency. The unfinished business thing is part of it, a little bit.”
Frankly, Lowry said enough on Tuesday to allow you to believe what you already believed before he spoke. It was a matter of confirmation bias: Whatever you thought before, it seemed as if he was screaming those parts. Anything that countered that was whispered.
“Everyone’s gonna have their own opinion,” Lowry said. “And it’s a good story for people to write and to have fun with. But we’ll see what happens. No one knows what the future holds. No one knows what comes with the next day. We all just have to live it every day and every moment. And that’s important, to just take it day by day and minute by minute, hour by hour, and live our lives like that. But it’s a cool story to write for people. I just hope they make me look really cool.”
That’s the thing: Whatever Lowry decides, to Raptors fans, it would be hard for him to ever look cooler.
This is the third time the Raptors have faced a free agent decision with Lowry. In 2014, Lowry quickly re-signed with the franchise despite coming perilously close to being traded that winter. Then in 2017, Lowry explored his options in free agency before ultimately returning on a three-year deal that was then extended one additional season, taking him to this third round of negotiations. For Lowry, the biggest difference in what he’s looking for now as compared to previously is stability for his soon-to-be teenage children.
“My kids being older, they’re at a point where stability is going to be key. They had some good stability in Toronto so far,” Lowry said.
The Raptors once again came close to moving Lowry at in March, but a deal could not be struck to send Lowry to a contender. Lowry’s stated goal is to win more championships, and that has never wavered. But what is unclear is if Lowry views the Raptors as a contender after an unfortunate season that saw them finish 12th, or if he would wants to go elsewhere for better odds. The Raptors could potentially sign-and-trade Lowry if he did want to move on.
Another factor for Lowry is the future of Raptors president Masai Ujiri, who is also a free agent. Reports are that Ujiri will most likely return, however his contractual status has lingered as a question mark dating back to the summer of 2019, when Ujiri should have been awarded with an extension after winning the title. Lowry and Ujiri have had rocky moments, but the six-time All-Star has come to respect Ujiri as a top executive and Ujiri’s future could impact Lowry’s own decision.
“Our relationship has grown from the time I’ve been here, to the time now. Our relationship has gotten better, put it that way. At the end of the day, and I told him, part of the reason I’m still here is because of him. Part of the reason I re-signed here twice is because of him, that’s a large part of why I’m able to be who I am and gotten to this point. So his decision, yes it will definitely factor into anything,” Lowry said of Ujiri’s contract negotiations.
It’s not only money, though. A few minutes later he added: “I want more championships, that’s always been the goal. Yeah, the money comes with that and you’ll get paid, but championships are a big key into why I play this game.”
Taken together, those two comments should be music to the ears of Raptors fans and a big, fat, obvious, flashing neon signal to the Raptors; they can keep him if they want to.
If Lowry was determined to go ring hunting and let the league know he would play for the mid-level exception – contracts that start in the $10 million a year range and can be offered by teams already over the salary cap — the list of contending teams that would rush to sign him would include virtually all of them.
But presuming Lowry is looking for a deal at least somewhat in the vicinity of the $31-million he was making this past season, the list of teams that can make a serious offer gets a lot shorter.
He’s been linked to the Miami Heat since he was a free agent the last time, back in 2017, and the Heat were his preferred destination had the Raptors moved him at the trade deadline. But Miami didn’t exactly move heaven and earth to grab Lowry in March and the likely cap space they can generate for a deal this summer would start in the $20 million range.
Who’s to say they even want to use all that money on Lowry as they head into a season in which they’ll have extended Jimmy Butler, will have Bam Adebayo’s max extension kick in and likely had to throw some serious money at restricted free agent Duncan Robinson.
After that? The New York Knicks and Dallas Mavericks can each create enough room for a max-type salary. The Knicks could convince themselves that Lowry could do for their young team what Paul did for the Suns this year, but there’s no guarantee they would want to go that route. The Knicks chose not to bid on VanVleet – a younger version of Lowry – this past summer and might be planning to keep the powder dry for the summer of 2022, when the free-agent market is deeper with the kind of A-List names that might be up for the challenge of taking the Knicks over the top. The Mavericks have needs, but between Doncic and Jalen Brunson, ball-handling isn’t likely a high enough priority to use their cap space on, but we’re speculating.
The key here is the Raptors can shut all that noise down in a hurry by doing what the NBA’s collective bargaining agreement provides for: allowing incumbent teams to go over the cap to sign their own players and to pay them more to stay than other teams can entice them to leave.
KLOE rode less often this past season, but injury and “rest” shenanigans aside, the greatest ever Toronto Raptor only burnished his legacy with what was, sneakily, one of Lowry’s best seasons of his career — he posted his third-highest effective field-goal percentage ever, for example.
The eye-test suggests that Lowry may have lost a small step on the defensive end, but the risk that he’s about to engage in a major drop-off as he enters his age-36 season seems as small as it could be for a six-foot point-guard about to enter… his age-36 season.
So, is Lowry staying or going? The tea leaves say a million things. Why would Lowry sell his house if he was going to stay? (Because of profit.) Why would the Raps not trade him and then let him rest for the majority of the season to keep him fresh for next year? (Because they’re a classy organization and had no desire to possibly injure someone before their last big payday.) Where else could Lowry even go? (The Heat, for one, but you know what, don’t answer that one just yet.)
I still lean towards Lowry staying simply because there aren’t that many big money landing places that would be willing to pay Lowry what he’s worth. If the trade market told us anything it’s that the league may still under-value what he brings. Now, does Victor Oladipo’s total no-show in Miami make me nervous? Yes. If Chris Paul somehow finds a better deal somewhere else, would Lowry fit well in what the Suns are trying to do? Sure. I just feel that, in the end, the money and the fit may work out best back in Toronto.
Of course, Kyle might be ready for a new adventure, and if he is, I say time to start building the statue*.
(*I’m cheating here, of course, because Lowry’s Raptors jerseys will never go on Kijiji. I do think he’s more likely to leave than Trent.)
Even at 35, he’s shown he can impact the game at a high level and he wants his next, and perhaps final, big NBA contract to reflect that. Only three players have ever signed a deal worth at least $20 million for multiple years at age 35 or older: Kobe Bryant, Dirk Nowitzki and LeBron James. Lowry intends to add his name to that prestigious group, but it’s hard to see him getting that kind of money or term without the Raptors, who can offer more than any other team, or without their help in a sign and trade.
He acknowledged that there might be some “unfinished business” for him in Toronto, coming off a year in which the team missed the playoffs and spent the entire campaign playing its home games in Tampa. He also noted that the future of team president Masai Ujiri, whose contract is also set to expire, could also be a factor in his decision.
Where Lowry ends up will depend on how he weighs his priorities, what his market looks like in August and in which direction he and the Raptors decide to go when the time comes.
“I’m older [than when I was a free agent in 2017],” Lowry said. “That’s one. [I’m coming] off one of the most difficult years in NBA history, with COVID, the relocation [to Tampa]. And then also this is way different with my family, and my kids being older. My kids, they’re at a point where stability is going to be key. They’ve had some good stability in Toronto so far, and we’ll see what happens with that. It’s a big difference because of my family situation, where I’m at in my career. I want more championships, that’s always been the goal. Yeah, the money comes with that and you’ll get paid, but championships are a big key into why I play this game.”
The Raptors also have to decide what’s best for them. Re-signing Lowry would cut into most, if not all of their salary cap space. It’s no secret they’ve prioritized that flexibility; it’s motivated almost everything they’ve done, or haven’t done, over the past few years, from declining to offer Serge Ibaka a second season of guaranteed money last fall to signing players to short-term deals with team options. They’ve had the summer of 2021 circled on their calendar for a while.
But things change, that’s why there’s value in remaining flexible. Their presumed target, Giannis Antetokounmpo, is no longer on the board. Several other stars have also signed contract extensions, including Paul George and Jrue Holiday. Victor Oladipo is hurt. Suddenly, this crop of free agents has thinned out and Lowry projects to be one of the best players available.
They could bring him back, retain Gary Trent Jr. (a restricted free agent) and add a few depth pieces to the young core of Pascal Siakam, Fred VanVleet and OG Anunoby, as well as their lottery pick, which will more than likely fall in the top 10 of July’s NBA draft. But is that team good enough to get them back to where they want to be?
You could make the argument that they’re better off going younger and using that $20 million or so of cap space elsewhere. You could also argue that Lowry deserves to spend his final seasons chasing another ring or two with the Lakers, Clippers, 76ers or the Heat.
“Of course, Toronto’s always going to be home to me,” Lowry said. “It’s a situation I would love to be in, and if it works out, it works out. If not, then we make choices on what’s best for myself and my family.”
But make no mistake: They have been the faces of the franchise:
“Kyle Lowry is obviously the greatest Raptor of all time, and No. 2 might be Masai,” Fred VanVleet said Sunday.
It hasn’t always been easy and certainly not all sweetness and light. They had a long, difficult discussion in the middle of the team’s championship run when Ujiri challenged Lowry to step up or be moved out. There was a time in 2013 when Lowry was all but packed up and out of town, with Ujiri more than ready to ship him to the New York Knicks, the best move the president never made. They got in each other’s faces over contract negotiations, and they went months without talking after Ujiri traded away DeMar DeRozan, who was and is Lowry’s best friend in the game.
But that’s all part of the maturation of Lowry and the leadership role he has grown into over nine seasons with the Raptors. It’s an oft-told tale — he went from an impetuous young kid to a father of two in his time with the Raptors and morphed into the soul of a championship organization.
It reached another zenith this year at the trade deadline in March when Lowry could have been moved.
“There’s a reason they decided not to, and … as a man, I respect it. (Ujiri) was in open communication with me about it. If I said something in January (believing in the team) that I truly believed, I stuck with it. Those guys had the final decision, and they made the call not to. I roll with what they’ve done the last eight years. I haven’t been happy about all the things they’ve done, but I rolled with it and figured it out.”
The collaborative nature of his relationship with Ujiri and the organization even factored into the decision for him to sit the final seven games of the regular season, including two crucial games that might have kept Toronto’s faint playoff hopes alive.
“That was a decision that we all made collectively. I wasn’t mad at the decision,” he said. “A lot of things went into that. I wouldn’t say it was just one thing. I think it was a multiple amount of things that went into that. But it was a decision that was made collectively.”